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5-hydroxytryptamine hydrochloride is an indole derivative, called 5-HT hydrochloride. It is first found in serum, also known as serotonin. It widely exists in mammalian tissues, especially in the cerebral cortex and synapses. It is also an inhibitory neurotransmitter. White powder, soluble in water, stable under normal temperature and pressure, sealed in a dry and cool place, away from strong oxidants.
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Chemical Formula |
C10H13ClN2O |
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Exact Mass |
212 |
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Molecular Weight |
213 |
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m/z |
212 (100.0%), 214 (32.0%), 213 (10.8%), 215 (3.5%) |
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Elemental Analysis |
C, 56.48; H, 6.16; Cl, 16.67; N, 13.17; O, 7.52 |
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melting point 149 – 154 °C ( lit. ), Storage conditions 2-8 ° C, Solubility H2O: 17 mg / mL morphological powder, Color white to off-white, Water-soluble, Sensitive Light Sensitive & Hygroscopic, BRN 3570963, stable, but light-sensitive and hygroscopic. Incompatible with oxidizing agents. , InChIKeyMDIGAZPGKJFIAH-UHFFFAOYSA-N, Hazardous Mark Xn, Xi, Hazard, Hazard category code 20 / 21 / 22-36 / 37 / 38, Safety instructions 22-26-36, Transport number of dangerous goods UN2811, WGK Germany 3, RTECS NM2571000, F 3-8-10, HazardClass 6.1, Packing Group III.
Its role in sleep is controversial: early studies showed that serotonin can promote sleep, but the final research paradigm has shifted to the wake-up function of serotonin. 5-hydroxytryptamine, as a neurotransmitter, can participate in various central nervous system activities and is a messenger of pleasure emotions, affecting almost every aspect of brain activity. With the rapid development of health products, 5-hydroxytryptamine is also increasingly used in health products. Nowadays, 5-hydroxytryptamine is widely used in many large health companies in Europe and America.
Some studies have shown that serotonin promotes sleep, but other studies have shown that serotonin producing neurons are most active when awake, when they release a large amount of serotonin. However, it is recognized that it is an important neurotransmitter. It plays a role in the brain, enabling us to feel happy and happy. Therefore, it is also called "happy neurotransmitter". It participates in a wide range of physiological functions of the human body, including regulation of brain memory, cognition, emotion, learning and addiction. The disorder of this system may lead to a variety of mental diseases, such as depression, schizophrenia, etc.
5-hydroxytryptamine hydrochloride (CAS number 153-98-0), as the hydrochloride form of 5-hydroxytryptamine (5-HT), is a key compound in neuroscience, pharmacology, and biomedical research. Its molecular formula is C10H12N2O · HCl, with a molecular weight of 212.68. It is a white to off white crystalline powder at room temperature and is easily soluble in water (17 mg/mL) and acidic solutions.
The core value of 5-HT · HCl probes lies in their specific targeted activation ability towards the serotonin receptor family. Seven major categories and 14 subtypes of 5-HT receptors (5-HT1-5-HT7) have been identified in mammals. Except for 5-HT3, which is a ligand gated ion channel receptor, the rest are members of the G protein coupled receptor (GPCR) family. Different subtypes of receptors have significant differences in distribution in brain regions, coupled proteins, downstream signaling pathways, and biological functions, forming a complex regulatory network of the serotonin system.
The active ligands dissociated from exogenous 5-HT · HCl can accurately recognize the extracellular ligand binding domains of various subtypes of receptors, achieve specific binding through molecular conformation matching, and do not cross activate other neurotransmitter receptors. Among them, 5-HT1 and 5-HT5 receptors mainly couple with Gi/o proteins, mediating inhibitory signaling; 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors mainly couple with Gs and Gq proteins, mediating excitatory signaling;
5-HT3 receptors directly regulate cation influx and rapidly mediate postsynaptic potential changes. 5-HT · HCl can achieve differential activation of receptors with different affinities through dose gradient regulation, providing precise intervention tools for studying the independent functions of different receptor subtypes, which is a probe advantage that other non-specific agonists cannot achieve.
Controllable dose-response and reversible regulatory characteristics
As a standardized experimental probe, 5-HT · HCl has excellent dose-response linear relationship and reversible action, fully meeting the quantitative needs of basic research. In vitro cell experiments and brain slice incubation experiments, low concentrations of 5-HT · HCl (10-100nM) can preferentially activate high affinity 5-HT1 and 5-HT7 receptors, simulating the basic regulatory role of endogenous neurotransmitters under physiological conditions;
Medium concentrations (100nM~1 μ M) can activate mid affinity receptors such as 5-HT2 and 5-HT4, mediating neural plasticity regulation; High concentrations (1-10 μ M) can fully activate all receptor subtypes, simulating the state of excessive activation of serotonin signaling under pathological conditions.
At the same time, the action of 5-HT · HCl can be rapidly blocked by specific receptor antagonists, and the signal activation effect is completely reversible,
without causing permanent damage to nerve cells, which can meet the scientific research needs of repeated interventions, control validation, and gradient experiments. Compared with irreversible intervention methods such as gene knockout and viral interference, 5-HT · HCl small molecule probes can achieve dynamic intervention of "instantaneous activation sustained regulation rapid termination", which is more in line with the real physiological dynamic regulation of neurotransmitters.
5-HT · HCl has a single chemical structure, no fluorescence spontaneous interference, and no electrochemical impurity interference. It can perfectly adapt to current mainstream neurobiological detection technologies, including gene coding fluorescent probe imaging, electrochemical real-time detection, Western blot protein quantification, qPCR gene detection, immunofluorescence localization, patch clamp electrophysiological recording, in vivo fiber optic imaging, etc.
In recent years, the new generation of 5-HT fluorescent probes and iSeroSnFR high-sensitivity detection probes developed based on the GRAB strategy can be combined with 5-HT · HCl intervention experiments to achieve visual capture of dynamic changes in serotonin signals at the cellular, tissue, and in vivo levels, greatly improving the accuracy and depth of molecular mechanism research.
Core neurobiological and molecular regulatory mechanisms mediated by 5-Hydroxytryptamine Hydrochloride
5-HT · HCl activates different subtypes of GPCR receptors, initiating differentiated downstream signaling cascades that form the molecular basis for regulating neuronal function. One is the inhibitory pathway mediated by Gi/o protein: after activating 5-HT1 and 5-HT5 receptors, Gi/o protein inhibits adenylate cyclase (AC) activity, reduces intracellular second messenger cyclic adenosine monophosphate (cAMP) concentration, inhibits protein kinase A (PKA) phosphorylation activation, reduces presynaptic neurotransmitter release, lowers neuronal excitability, and participates in emotion suppression, pain relief, and neural discharge homeostasis regulation.
Secondly, the excitatory pathway mediated by Gq protein: 5-HT · HCl activates 5-HT2 receptors, which in turn activates phospholipase C (PLC) and hydrolyzes phosphatidylinositol diphosphate (PIP ₂) to produce inositol triphosphate (IP ∝) and diacylglycerol (DAG). IP H3 binds to endoplasmic reticulum IP H3 receptors, promoting the release of Ca ² ⁺ from the endoplasmic reticulum calcium pool, increasing intracellular calcium ion concentration, and activating the calmodulin kinase (CaMK) family;
DAG activates protein kinase C (PKC), initiates downstream MAPK/ERK signaling pathway, regulates neuronal proliferation, differentiation, and synaptic plasticity remodeling.
Thirdly, the excitatory pathway mediated by Gs protein: after activating 5-HT4, 5-HT6, and 5-HT7 receptors, adenylate cyclase is activated, cAMP content is increased, PKA is activated, CREB transcription factor phosphorylation is regulated, neuroprotection, synaptic protein expression, and cognitive memory related gene transcription are promoted, which is the core pathway of neural plasticity regulation.
Ionic Channel Regulation and Neuronal Electrophysiological Mechanisms
5-HT · HCl can regulate neuronal ion channel function directly and indirectly, altering neuronal excitability and synaptic transmission efficiency. On the one hand, it specifically activates 5-HT3 ligand gated ion channels, directly mediating the transmembrane flow of Na ⁺ and K ⁺ cations, rapidly inducing postsynaptic depolarization potentials, achieving millisecond level rapid neural signal transmission, and participating in physiological processes such as brainstem reflexes and rapid emotional responses.
On the other hand, through the downstream signaling pathway of G protein, the opening probability and dynamic characteristics of voltage-gated potassium channels, calcium channels, and sodium channels are indirectly regulated, and the resting potential and action potential firing frequency of neurons are regulated to maintain the steady state of neural circuit electrical activity.
Electrophysiological experiments have confirmed that physiological concentrations of 5-HT · HCl can stabilize the firing rhythm of hippocampal and cortical neurons and inhibit neuronal overexcitation; Under high pathological concentrations, it can induce abnormal neuronal discharge, leading to neural circuit disorders, providing direct experimental evidence for analyzing the electrophysiological mechanisms of pathological states such as anxiety and mania.
Neuroplasticity is the core foundation for the nervous system to adapt to changes in internal and external environments, mediate learning and memory, and regulate emotions. 5-HT · HCl is a key probe for studying the molecular mechanisms of synaptic plasticity. It activates the downstream CREB/BDNF signaling pathway, promotes the expression of core plasticity proteins such as brain-derived neurotrophic factor (BDNF), postsynaptic dense protein (PSD-95), and synapsin, and regulates the dynamic remodeling of synaptic morphology, synaptic quantity, and synaptic transmission efficiency.
Meanwhile, 5-HT · HCl regulates the intracellular calcium ion homeostasis, affects the growth, maturation, and pruning of dendritic spines, and regulates the strength of synaptic connections between neurons. In the stage of neural development, it can mediate neuronal migration, differentiation, and neural network construction; In the adult nervous system, participating in the neural repair and emotion related neural circuit remodeling after stress injury is a core tool for analyzing the positive and negative regulatory mechanisms of neural plasticity and studying the molecular mechanisms of neural injury repair.
In recent years, basic research has confirmed that 5-HT · HCl can participate in the regulation of neuronal survival and apoptosis by modulating the oxidative stress pathway. Moderate concentrations of 5-HT · HCl can enhance the activity of neuronal superoxide dismutase and glutathione peroxidase, reduce the accumulation of reactive oxygen species (ROS), inhibit lipid peroxidation reactions, alleviate neuronal oxidative damage, and exert neuroprotective effects;
Excessive 5-HT · HCl can lead to overactivation of serotonin signaling, induce intracellular calcium overload, activate mitochondrial apoptosis pathway, upregulate Bax and Caspase-3 apoptosis protein expression, induce neuronal apoptosis and neuroinflammatory response. The discovery of this bidirectional regulatory mechanism relies entirely on the controllable gradient intervention of 5-HT · HCl probes, providing important molecular evidence for the study of the mechanisms of neurodegenerative diseases and stress-induced nerve injury.
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A preparation method for 5-light tryptamine hydrochloride, specifically involving the efficient synthesis of 5-light tryptamine hydrochloride through two steps of addition reaction and reduction reaction using 5-light group noise and nitroethylene as raw materials. The production of 5-light tryptamine hydrochloride by this method is a high yield, low cost, low waste, good product purity, and suitable for industrialization.
1. A preparation method for 5-light tryptamine hydrochloride, comprising the following steps:
S1: Add solvent to the reaction bottle, add 5-light base noise, add nitroethylene, and conduct a temperature rise reaction with central control tracking: after the reaction is completed, concentrate, reduce temperature and crystallize, filter, and dry the filter cake to obtain intermediate 1;
S2: Add the solvent to the high-pressure vessel, add intermediate 1, add catalyst, replace it with nitrogen, and then introduce hydrogen gas to control and track the temperature rise reaction; After the reaction is completed, filter under pressure and concentrate the filtrate to 1000: add EA to the residual solution, pass through hydrogen chloride gas, filter, wash the filter cake EA, and dry to obtain the product 5-light tryptophan hydrochloride.
2. A preparation method for 5-light tryptamine hydrochloride as claimed in claim 1, characterized in that in S1, the solvent is one of toluene and benzene.
3. A preparation method for 5-light tryptamine hydrochloride as claimed in claim 1, characterized in that the reaction temperature in S1 is between 50C and 110C.
4. A preparation method for 5-light group tryptamine hydrochloride as claimed in claim 1, characterized in that in S1, the molar ratio of 5-light group noise to nitroethylene is 1:1 to 1:3.
5. A preparation method for 5-hydroxytryptamine hydrochloride as claimed in claim 1, characterized in that the solvent in S2 is one of methanol, ethanol, isopropanol, tetrahydrofuran, or acetic acid acetic acid.
6. A preparation method for 5-light tryptamine hydrochloride as claimed in claim 1, characterized in that the reaction temperature in S2 ranges from 20C to 60C.
7. A preparation method for 5-light tryptamine hydrochloride as claimed in claim 1, characterized in that the catalyst in S2 is one of Raney nickel and Pd/C.
8. A preparation method for 5-light tryptamine hydrochloride as claimed in claim 1, characterized in that the amount of catalyst in S2 is 1% to 10% of the mass of intermediate 1.
Frequently Asked Questions
Q1: Does the discoloration of 5-hydroxytryptamine hydrochloride aqueous solution result in complete loss of receptor binding activity of the product?
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A: The indole quinone polymer generated by oxidation has no receptor activation effect, which not only fails but also interferes with the baseline of in vitro cell experiments.
Q2: Why can't free 5-HT alkaloids and 5-hydroxytryptamine hydrochloride be directly replaced and administered with equal quality?
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A: The molar mass of the two is different, and there is a difference in the dissociation degree of the aqueous solution. The effective concentration of 5-HT under the same weight is inconsistent, resulting in experimental dose deviation.
Q3: Low temperature can delay degradation when preparing buffer solution, but repeated freezing and thawing can accelerate deterioration?
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A: The freeze-thaw process induces local pH fluctuations and phase separation, promoting indole epoxidation. Single package freezing is better than multiple thawing and retrieval.
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